Imidazoline derivatives and process



' amass MIDAZOLINE DERIVATIVES PROCESS Hans S. Mannheimer, New York, Y assignor to John J. McCabe, Jr. and HansS. Mannheimer, as joint venturers No Drawing. Application March 26,1956, Serial No.'73,630

Claims. (Cl. 260--309.6)

Thisinvention relates. to novel compositions and to methods for producing .them.. In one of its more specific aspects the invention is directed to novel derivatives of that class of compounds which may be prepared by following the methods described in my copending application, Serial No. 521,393, fi1ed July 11, 1955 and having the following general Formula I: I

wise being hydrocarbon of 2-4 carbon atoms, (f) aliphatic keto groups, each of said groups having-a single-keto linkage therein and otherwise being hydroxy substituted hydrocarbon of 2-4 carbon atoms; M is an alkali metal and preferably sodiumor potassium which are obvious equivalents, J 5; Said compounds of Formula I-may be derived from the metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates, examples of which aredisclosed in my U. S. Patent2,528,378, and which I shall hereinafter refer to as cycloimidates. I vSaid cycloi'midates having the following general formula;

if R, R z'{and M have heretofore been defined. I Themethods tor rp aduc ag. said i yc m da fi and illustrative examr p a nl m .tf a d -cycloimidates;arei all of;

nited States Patent-O 2,781,353 Patented Feb. 12, 1957 ice 2 the cycloimidates disclosed in said patent which is made part hereof.

cycloimidine by reacting one-mole of a monocarboxylic acid, having at least 4 and preferably 4-18 carbon atoms in its radical'connected to its COOH group, with one mole of aminoethylethanolamine, known in said patent and herein as Reactant A. Then one mole of said cycloimidine is reactedwith one mole of a monohalocarboxylic, acid, such as monochloracetic acid, monochlorpropionic acid, monochlorlactic acid, etc., in the-presence ofa f xed PI'Q'. portion of caustic soda, all described in; said patent, to produce said cycloimidates. 'Such cycloimidates are produced because of the marked preferential of the reactants and because oi the mole proportion of reactants being one to one. 7

As disclosed in my application 521,393, ,said cycloimidates, under certain controlled conditions, maybe reacted with one of said monohalocarboxylic acids to replace the metallic element M of the R2OM group thereof with and Ra-COOM group: 7

Still another method which may be employed to produce said compounds of Formula I'is to heat together at approximately 100 C. one mole proportion of said cycloimidine and an aqueous solution at a pH of about 13 produced by previously combining at a temperature'no greater than 20 C. 2 moles Qf said monohalocarboxylic acid, having 1-4 carbon atomsin its hydroxy substituted hydrocarbon group, such as CHzCHOH orin its unsubstituted hydrocarbon group, such as C Ha C Hs, 'CtHs, and approximately 4.5-5 moles of caustic soda; The mass is maintained at said temperature of approximately 100"" C. until the pH thereof decreases to the range of approximately 8.8-9.3. V V i The following are illustrative examples given merely. for the purposes of specifically illustrating how some of" the compounds of Formula I may be produced, all parts being given by weight unless otherwise specified: V

placed in a reacting vessel and are heated sufiiciently to melt'thelauric acid whereupon an agitator located therein is. started andmixes and maintains these components in mixed condition. While being constantly agitated the mix isheated under vacuum of about 110 mm. pressure for about 3 hours while gradually raising the temperatune to 170 C. During this period-l8 parts of water have been-distilled 01f. Then the temperature of'the entire mass is gradually raised to 220 C.'over a period of about 2 hours While the mercury. pressure has been de-i creased to a value no greater than 30 mm. Under these conditions 18 more parts of water are distilled ofi'leaving behind in the reaction mass a 100% pure product which is a disubsti'tuted cycloimi'dine'which .is alight coloredviscous liquid at. room temperature. .Then this reaction product is allowed to cool at room'temperature and the entire mass is added to a previously' prepard solution produced by adding 192 parts of monochlorac'etic acid u and 180 parts of caustic sodato 600 parts of water. This solution wasprepared and maintainedxat a temperature below; 20 C. before the addition of said disubstituted cycloirni dine. This mixture is heated to C. and main? tained "at-this ;temperature for 2 hours. .During this "period the-pH-of the mir'is reduced from-approximately 13 .10, 8.8-9.3. At the end of. this eriod-the of this mass is no longer subject to change by continued heating at sa d. empe urean a. amp of t tesultantrmduct s -w ter ;.s olu le to espark ng lear solution; At the end of this period themass consists chiefly of awater 7 solution of a compound hereinafter known as product A and having the following formula:

CH2 N/ CH2 1 omr-o-om-oooNa Girliha- 'N/ ljom-C ONa Example A,1

200 parts of lauric acid and 104 parts of reactant A are placed in a reacting vessel and are heated sutficiently to melt the lauric'acid whereupon an agitator located there his started-and mixes and maintains these components in mixed condition. While being constantly agitated the mix isheatedunder vacuum of about 110 mm. pressure for about 3 hours while gradually raising the temperature to 170 C. During this period 18 parts of water have been distilled off. Then the temperature of the entire mass is gradually raised to 220 C. over a period 7 Example C 172 partsof capric acid and 104 parts of reactant A 1 are heated and reacted under the same condition as given of about 2 hours While the mercury pressure has been decreased to a value no greater than 30 mm. Under these conditions 18 more parts of water are distilled off leaving behind in the reaction mass a 100% pure prodnot which is a'disubstituted cycloimidine which is a light colored viscous liquid at room temperature. Then this reaction product is allowed to cool to room temperature and the entire mass is added to a previously prepared solution produced by adding 96 parts of monochloracetic acid and 90 parts of caustic soda to 300 parts ofwater. This solution was prepared and maintained at a temperature below 20 C. before the addition of said disubstituted cycloimidine. This mixture is heated to 95 C. and maintained'at this temperature for 2 hours. During this period the pH of the mix is reduced from approximately 13 to 8-8.5. At'the end of this period the pH ofthis mass is no longer subject to change by continued heating at said temperature and a sample of the resulting product is water-soluble to a sparkling clear solution which clouds upon standing. Then to said reaction mass there is added additional parts of caustic soda dissolved in 21 parts of water and heating is continued to maintain said mass at about 95 C. for an additional 1 hour.

At the 'end of that period said mass, known asTmass X, is cooled to room temperature and then there is added thereto a previously prepared solution produced by add ing 96 parts of monochloracetic acid and '80 parts of caustic soda into 300 parts of water while'maintaining same at a temperature no greater than20 C. and preferably at about 15 C. The resultant mixture of said mass and said-solution is then heated to and maintained at about 100 C. for about 1 2 hours. In that period, the pH of the resultant product'will have been reduced from approximately 13, that of the original mixture, to approximately 8.8-9.3. Then the resultant product is cooled to room' temperature and consists chiefly of an aqueous solution-of a reaction product, identical with that of Example A, with the amount of water in said solution being slightly greater than that of thesolution thereof in Example A. i

Example B All of mass X of Example A-l may be cooled to room temperature and there is then added thereto a solution consistingof 40 parts of caustic soda dissolved in 40 parts of Water. Then to said" mixture there are added 80.5 partsof chlorhydrin. .This mixture is heated over a period of '1 hour to 95 C. The mass is subsequently maintained at this temperature of" 95 C. until there is no change in pH, this taking approximately 2 to 3 'hoiirs,

The resultant mass is then cooled to room temperature and mixed with a previously prepared solutionproduced in Example A, and 240 parts of the disubstituted cycloimidine produced thereby are introduced into a solution of 220 parts of monochlorpropionic acid and 190 parts of caustic soda in 500 parts of water prepared and maintained below 20 C. The resulting mixture is then heated under the same conditions as outlined in Example A until the resulting product forms sparkling clear aqueous solutions and is no longer subject to pH change in continued heating. The mass consists chiefly of an aqueous solution of a compound hereinafter known as prodnot C and having the following formula:

l o,rn-o 02114-0 o 0 Na CnHm- N i C2H4 C O O N a Example D 282 parts linseed fatty acid and 104 parts reactant A are treated in the same manner as described in Example A. The entirereaction product is then processed with an aqueous solution jofv 192 parts monochloracetic acid and parts of caustic soda previously made and maintained below 20 C. and subsequently processed in the mannerof Example A to produce reaction product hereinafter known as product D and having the same formula as that of ExampleA, except the C1'1H31 is substituted for C I-I25 therein. 7

Example E 116parts-of caproic acid and 104 parts of reactant A are'condensed in the manner as described in the previous examples and theresulting reaction product is subsequently processed in the same manner as that set forth in theprocessing of the disubstituted.cycloimidine of Example. D. Thereaction product is hereinafter known as-p'roduct E and has the same formula as that of. Example A, except that "C5H 9 is. substituted for CriHzs' therein. a

- Example F in the previous Example A and there is produced a product hereinafter known as product F and having the same formula as that of ExampleC, except that CrvHas is substituted for Cal-I19 therein. 1

-Example i 290 parts dodecyl benzoic acid and 104 parts of reactant A i ondensedj in the manner described in Example D sass afid ussssaltantnteaus' ahama f Example D wherein there is prpduced a compound hereinafter known as Product S end-having the same formula as that of Example A, except that C12H25C6H4 is substituedfonCnHza-therein. 7

Example H and about 2 moles proportion of caustic soda in' about 3 moles of water and such mixtures are maintained at about 100 C. for approximately} hours whereupon the pH thereof decreases from 13 to about 8.8-9.3 to provide compounds which are the same as those of Examples 10-14 of said patent exceptrthat the sodium atom of the R-ONa groups thereof are replgg iqbll Cl-ia CQQNa, and an illustrative example of this is such group'of Example 10 having its sodium n tpnnso replaced to become CHzCHOHCHzQCHa QQONa. i r

V A largenfimbe'r of other specific compounds may be produced by using starting compounds other than those ned: i an .o gba efmaaidssx mple n d t ri s therefrom in the radical R. Also other specific compounds may be produced by using'a"monohalocarboxylic acid othenthanithe specific ones employed in the aforesaid examples.

Prior to this invention, it was known that cationic surface active agents and anionic surface 'activeagents when together in 'aqueous solution resulted in the production or formation of water-insolublecompounds; and that adding an anionic.surfaggactive agent to an aqueous solution of another anionic surface actiye agent resulted in a mere physical combinationofsaid agents andthat no reaction would occur between them.

Said compounds of Formulal normally behave anion ically in aqueousisolutionsmaving a.pH)-above"7, and consequently it was expected that when in aqueous solution vtogether with anionic, surlglarce ,agentathat they ,would be combined physically'only and that no other reaction would occur therebetween. In the course of my experimentations, Ihavepiscogered that said. pompounds -.of Formula I could be reacted with ertain anionic surface active agents at a pH above 7 to prod uce water-soluble reaction products. Not only did I make said discovery, but I furthendiscoveredthat'water solutions of such reaction products had viscosities greater...tba n. cgr responding aqueous solutions of thepornppundsof Formula I andsalso exhibited better foamingcharacteristics than did said com pounds of Formula I imvery lowdilutions under extreme water hardness conditions; Said reaction products are non-toxic and non-irritatihgit'o' the human skin. They tergency and surface actigetproperties and capable of pro;

viding volrnninops and stable foams in aqueous solutions, and whichaqueou's solutions are substantially nonirritating to the skin and eyes ofinormal hurnan beingsi" wherein R3 is selected from the group consisting, of (g) aliphatic and aliphatic-aromatic -hydr'ocarbon'radicalsof -6 l8 carbon atoms,-with the aliphatic-aromatic hydrocarbon radicals, each having an aliphatic radical of'at least 6 carbon atoms; R4 is seletned from the, group consisting of (h) aliphatic hydrocarbon gro upsyof 1 -12 carbon atoms, (1) hydroxy substituted aliphatic hydrocarbon groups of 1-12 carbon atoms, (j) aliphatic ether groups,

each of said groups having at least one ether linkage therei in, and otherwise being hydrocarbon of 2-12 carbon atoms, (k) hydroxy substitutedaliphatic ether groups, each of said groups having at least one ether linkage therein, and otherwise being hydroxy substituted hydrocarbon of 6-12 carbon'atoms, (l) aliphatic groups, each group containing CONH- and otherwisebeing hydrocarbon of 2-12 carbon atoms; ,X is a radical selected from the group consisting of SO3 and 08,03; R, R2 andsM have heretofore been defined.

According to this invention, I react a compound of Formuia I with a compound of-Formula II to provide the novel and highly useful compounds of Formula HI. In

, general this reaction is carried out in a solution containing compounds I and II and ,to which asquantityrof an acidic chloric, sulphuric or'its equivalent has been added to lower the pH of the solution to a value of approximately 7 to approximately 9 and while maintainingthe-mass at a temper'ature between approximately -200 F. 'In this reaction under the aforesaid, conditions, compounds of Formula III are produced and have highwater-solubility despite the fact that R3 has '6 or more ;carbon atoms. Such compounds of Formula III have unexpectedlyhigh 7 water solubility, while the corresponding salts of cationic compounds are water insoluble. The resultant solution can be used directly as a surface active agent, wetting agent or detergent for, the purposes indicated for the cycloirnidates. While. the quantities of, the, compound of Formula I and compound of Formula II maybe equimolecular for good yield of compounds of Formula III, I may employ an excess .o'f eitheriand in general the mole ratio for compound of Formula Ito compound or Formula II may be 2 moles of the former to 1-3 moles of the latter.

' One of the specific methods which I prefer to employ in carrying out an'aspec't of this invention is to first dissolve a compoundof Formula I in water and then 6 thejpHthereof is adjusted to approximately 12-13 (measured electrically) by the addition of aqueous v g M caustic soda if required. The temperature of said solu- Pe a na llli fiilfl lli fii lkfia sl srahutilitysie I gents,,s u ch'as for car washing, dish washing, clothes wash? egeaqtod twithtone .or;:1 com- 'added thereto to reduce the pH thereof to a value below 10 and in the range of approximately 7 to 9, and

preferably of approximately 8.2 to approximately 8.7. At the endofithe acidic agent.additiQmJhe stirring is continued and the temperature of the mass maintained for about 10-20 minutes after which the solution is allowed to cool and is a finished product,

The following are specific examples msrnygiven by- '2 V way of illustrating the invention and are not to be taken ORMULA F NOVEL I tEACTIOtI'PRQDU CI by way of limitation, all parts being given by weight I I I on: unless otherwise specified. I (Io-m I I Example 1 o,Ht=o'-oml-o0om' An aqueous solution of 480 parts of Product A in CoH1n -N 720 parts of water is heated approximately 140 F. and C its pH adjusted to 12-13 (measured electrically) by the 1 t I EHSOH 9 addition of aqueous caustic soda. While being constantly stirred and maintained at that temperature there is added 10 moH a solution of 350 parts of C11H2a-COO---C2H4---SOaNa Example V 525 parts of Product B in 950 parts of water. 360

in 525 parts of water. Then while stirring and temperature is maintained there is added thereto between 15 parts of I about 30-40 parts of hydrochloric acid solution (32%) C9H19-COO--C2H4-OSOa-Na' whereby the pH ofsthe mass is lowered to a value in l 1 the range of 8.2 to 8.7. Stirring is continued and the 602mm of water a 1 temperature maintained for about 10 minutes more. v 0F NOVEL'REACTION PRODUCT The resultant product is a solution of the novel reac- 1 v 7 5 tion product having the following formula: I N OH:

I l o.H4-o-o,Htoon=-ooom /CE2 Cn j N OH1-C00Na T I n /C2H4 0 cm COOI\a CIIHII COO CIHI OSOI CuHaa- N\ g I Ont-000m p fi C H -COO-C H -SO 470 parts of product A in 720 parts of water. 400

parts of I 7 I I 7 Example 2 Ci1H2aCOO -CzH4CHOHOCl-Iz-OSOa-Na I I Employ the same procedure and components as set m 600 parts of t forth in Example 1, except that only 150 parts of FORMULA OF NOVEL REACTION PRODUCT C11H23-cOO- -C2H4- SO8N34 are used. In this inr stance the resultant product is a solution of the reaction product whose structural formula is shown in r Example 1 together with unreacted Product A used, in l i the approximate proportion of 2 parts of the former 40 0111123- 1N t V to 1 of the latter. 7 \CHs O0ONu Employ the same procedure as that set forth in Exam- 7 I V ple 1, but employ the components indicated in the fol- V *Q QBQ lowing Examples 3-18; the quantity of hydrochloric acid E l 7 solution (32%) is variable to lower the pH to values t indicated in Example 1 to obtain the reaction products 600 parts of product F- dissolved in 900 parts of water. of said Examples 3-18. V 500 parts of I Example 3 C1oH21--COO-C2H4NHCOCH2-'-SOa--Na 480 parts of product A in 720 parts of water. 310 in 600 parts of water. V parts Of FORMULA OF-NOVEL REACTION PRODUCT CsH17COO--CH2(CHOH)CH2CO3-Na 0g, in 460 parts of water. 7 r I a ,N om I I FORMULA OF NOVEL vREAC'lION PRODUCT I 1L I/VC:H4- -O C.HaCOONa OnHa r- N\ r J oim oo omt N om uwooo-oimunooonr o,

/C2H4OICH1C0ONB Cum? N Example 7a I V v v fi480 parts of Product A in 720 par-ts of water. 530 parts I I I o I V CEHWCOVWCESOHOH)011F803 CuH23-COOC2H4NHCOCH2OSO3 I in 650 arts of water. 7 Example 4 p I I V, I FORMULA OF NOVEL REACTION PRODUCT 450 parts of product C in 800 parts of water. 475 CH parts of r a I N CH| onms-ooo- -onr-h-onrosoil-Na 011321- -N\ I CHP-GOONB 7 Colin-QC o o-clurfo;s ot

.parts of am le. ,i 480 parts of ProductA in 7 20 part s otwater. 360 parts of t V r C11H23COOCH2CH0HCH20S0a-Na 75 in 500 parts of water.

FORMULA or NOVEL REACTION PRODUCT (Emilia-ClOO-CHnCHOHCH -OSO; V p 1 Exajnpll V 525 parts of Product H dissolved in 800 parts of water. 500 parts of CeHm-COO C2H4OC2H4OCaH4-OSOsNa dissolved in 750 parts of water;

FORMULA OF NOVEL REACTION PRODUCT H2 7 N X orr; 1 i i 2 l' CRHA QO QHT CO QNQ CrsHtt- I T 7v i cliwcoona, 1

7 Example 9 7 430 parts of Product A i zzo parts of @420 in 650 parts ofwater. j v w FORMULA orrnovnnanaorropraopuom doukooons ,parts of V Er IiWQJ 480 Par-tact Brow??? in 720- hi assist 71o a which are shown herein merely as illustrative examples of reactants of Formula II to produce novel compounds of Formula III.

'It is to be understood that when either S0301 QSOs is.

used in the specificatidn or claims, it is meant to indicate either one or the other because of their obvious equivalency; it is also to be understood thatthe use of Na in the specification and claims is meant to indicate any of the other alkali metals because of their obvious equiv alency; and it is also to be understood that the CONH linkage when part of R4 11 the specification and claims is meant to indicate either it or NHCO because of their obvious equivalency.

It is also to be understood that instead of first adjusting the pH of the compound of, Formula I to 12- -13 before the addition of the compoundof Formula II, any other method may be employed to obtain the condition whereby the pH of the solution of I and II is at least 10 and preferably 10.5-11 before the addition of the acidic agent to lower the pH of the mass to approximately 7 to approximately 9. For example l and Il may be dissolved together and this solution'may by the addition of caustic 'soda when required have its pH adjusted to at least 10,

and then at l00200 F. is ready forthe addition of the acidic agent to lower its pH to approximately 7 to approximately 9. lf'desired, the required amount of acidic agent may be added either before or after the solution at pH at least 10 is brought to a -tempera-ture in the range of 100200 F. V a

Since certain changes in carrying out the aforesaid processes and certain modifications in the compositions which embody the invention may be made without departing from its scope, it is intended that all matter contained in the description shall be interpreted as illustrative and not in a limiting sense.

It is also to be understood that the following claims are intended to cover all the generic and specific features of the invention herein described, and all statements of the scope of the invention which as a matter of language be said to fall therebetween.

I claim: 7 I l. A novel compound of the following formula:

CH2 N om RaO-Rz-COOM rz-o-N ew-sex a in which R is a hydrocarbon radical of 4-18 carbon atoms;

R2 is selected from the class consisting'of-(q) aliphatic hydrocarbon groups of l-4 carbon atoms, (b) hydroxy substituted hydrocarbon groups of l r carbon atoms,

(c) aliphatic ether groups, each of said groups having asingleether linkage therein and otherwise being hydrocarbon of 2-4 carbon atoms, (d) aliphatic ether groups, each of said groups having a singie ether'lin'kage therein and otherwise being hydroxy substituted hydrocarbon of 2,4i.ca r bon atoms, (2) aliphatic keto groups, each of said groups having a single keto linlgage therein and otherwise being hydrocarbon of'24 carbon atoms, (1) aliphatic keto groups, each 'of said groups having a single keto linkage therein and otherwise being hydroxy substituted hydrocarbon of 2-4 carbon atoms; wherein R3 is selected from the group consisting of (g) aliphatic and.

aliphatic-aromatic hydrocarbon radicals of 6-13 carbon atoms; with the aliphatic-aromatic hydrocarbon radicals, each having an aliphatic radical of at least 6' carbon atoms;

R; is selected from the group consisting of (h) aliphatic hydrocarbon groupsofl-lZ carbon atoms, (1) hydroxy substituted aliphaticih'ydrocarbongroups of l- -l2 carbon fatoms, (j) aliphatic ether groupsge'ach of said groups having at least one, ether. linkage therein, and otherwise being hydrocarbon of 2-12 carbon-atoms, (lg)- hydroxy 11 substituted aliphatic ether groups, each'of said groups having at least one ether linkage therein, and otherwise being hydroxy substituted hydrocarbon of 2-12 carbon atoms, (1) aliphatic groups, each group containing -CONH and otherwise being hydrocarbon of 2-12 carbon atoms; and M isan alkali metal.

2. A novel compound of the following formula:

/Cs2 N CH2 ant-o on aa-oo 0-12-50;

in which R is a hydrocarbon radical of 4-18 carbon atoms;

R3 is hydrocarbon of 6-18 carbo-n atoms; and R4 is hydrocarbon of 1 -12 carbon atoms. 3. A novel compound of the following formula:

in which R3 is a hydrocarbon radical of 6-18 carbon atoms; and x is l-5.

5. A novel compound of the following formula:

6. A novel compound of the following formula:

I CH3 N/ CHa a I O:H4-OCHa-COONa CnH2s'C--N CHs-COONa 7. A novel compound of the following formula! I CH2 d N/ CHa l I oniononom-o-om-coom G1a s7- N-/ om-coon -O1al[a1-COOCnH4-S 0a 12. 8. The method comprising under pH conditions of approximately 7- to approximately 9 reacting with each other compounds of the following Formulas I and II:

FORMULA I 7 FORMULA n ro-coo-Rr-X M in which R is a hydrocarbon radical of 4-18 carbon atoms; R2 is selected from the class consisting of (a) aliphatic hydrocarbon groups of 1-4 carbon atoms, (b) hydroxy substituted hydrocarbon groups of 1-4 carbon atoms, (0) aliphatic ether groups, each of said groups having a single ether linkage therein and otherwise be-- ing hydrocarbon of 2-14 carbon atoms, (d) aliphatic ether groups, each of said groups having a single ether linkage therein and otherwise being hydroxy substituted hydrocarbon of 2-4 carbon atoms, (e) aliphatic keto groups, each of said groups having a single keto linkage therein and otherwise being hydrocarbon of 2-4 carbon atoms, (f) aliphatic keto groups, each of said groups having a single keto linkage therein and otherwise being hydroxy substituted hydrocarbon of 2-4 carbon atoms; wherein R3 isselected fromthe group consisting of (g) aliphatic and aliphatic-aromatic hydrocarbon radicals of 6-18 carbon atoms, with the aliphatic-aromatic hydrocarbon radicals, each having an aliphatic radical of at least 6 carbon atoms; R4 is selected from the group consisting of (h) aliphatic hydrocarbon groups of 1-12 carbon atoms, (i) hydroxy substituted aliphatic hydrocarbon groups of 1-127carbon atoms, (j) aliphatic ether groups, each of-said groups having at least one ether linkage therein, and otherwise being hydrocarbon of 2-12 carbon atoms, (k) hydroxy substituted aliphatic ether groups, each'of said'groups having at least one ether linkage therein, and otherwise being hydroxy substituted hydrocarbon of 2-12 carbon atoms, (l) aliphatic groups, each group containing CONH- and otherwise being hydrocarbon of 2-12 carbon atoms; M is an alkali metal.

9. The method comprising to a solution containing a compound of Formula I and a compound of Formula II both defined in claim 8, adding a quantity of an acidic agent to lower the pH thereof to a value of approximately 7 to approximately 9 and maintaining the temperature of the mass between about 100 F. and 200 F.

10. The method comprising to a solution whose pH i is at least 10 and containing a compound of Formula I and a compound of Formula H both defined in claim 8, adding a quantity of an'acidic agent to lower the pH thereof to a valueof approximately 7 to approximately 9 and maintaining, the temperature of the mass between aboutllOO? F. and 200 F. v

11. Themethoddefined in claim 8,'with the mole ratio of compound of Formula Ito compound of Formula II being 2 moles of the former to 1-3 moles of the latter.

12. The method defined in claim 9, with the mole ,ratioofcompound of Formula I to compound of Formula.

2,?81,3B 8 14 H being 2 moles of the former to 13 moles of the latter. 15, A novel command f h f ll wi f r la;

14. A novel compound of the following formula: on

:52 i-z cm N 5 H c,mo-om-co0N 0.H4-0-om 000M (my? N C11H:a -N

CH:C 0 GM:

CuHn-C(JO-CHaCHOHCHr-OSO;

CHg-COONB.

O HuC O O-CIH|NHC O CHr-OSOa 10 No references cited. 

1. A NOVEL COMPOUND OF THE FOLLOWING FORMULA: 